WO2022059740A1 - 表示素子用封止剤、その硬化物および表示装置 - Google Patents
表示素子用封止剤、その硬化物および表示装置 Download PDFInfo
- Publication number
- WO2022059740A1 WO2022059740A1 PCT/JP2021/034151 JP2021034151W WO2022059740A1 WO 2022059740 A1 WO2022059740 A1 WO 2022059740A1 JP 2021034151 W JP2021034151 W JP 2021034151W WO 2022059740 A1 WO2022059740 A1 WO 2022059740A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- mass
- meth
- acrylate
- display element
- parts
- Prior art date
Links
- 239000003566 sealing material Substances 0.000 title abstract description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 29
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 10
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 7
- 238000007789 sealing Methods 0.000 claims description 49
- 239000000565 sealant Substances 0.000 claims description 28
- 239000000758 substrate Substances 0.000 claims description 15
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 7
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 claims description 6
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 claims description 3
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 abstract description 7
- 239000010410 layer Substances 0.000 description 76
- 239000008393 encapsulating agent Substances 0.000 description 41
- 238000000034 method Methods 0.000 description 32
- 239000010408 film Substances 0.000 description 27
- 239000011347 resin Substances 0.000 description 27
- 229920005989 resin Polymers 0.000 description 27
- 238000001723 curing Methods 0.000 description 18
- 229910010272 inorganic material Inorganic materials 0.000 description 18
- 239000011147 inorganic material Substances 0.000 description 18
- 230000004888 barrier function Effects 0.000 description 16
- 239000000463 material Substances 0.000 description 13
- -1 norbornanediyl group Chemical group 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 11
- 150000002430 hydrocarbons Chemical group 0.000 description 11
- 239000003999 initiator Substances 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 7
- 239000012965 benzophenone Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 3
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 229910052581 Si3N4 Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 3
- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- BXSPZNVFEYWSLZ-UHFFFAOYSA-N (3-phenoxyphenyl)methyl prop-2-enoate Chemical group C=CC(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 BXSPZNVFEYWSLZ-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- HYQASEVIBPSPMK-UHFFFAOYSA-N 12-(2-methylprop-2-enoyloxy)dodecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCCCOC(=O)C(C)=C HYQASEVIBPSPMK-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- YWEJNVNVJGORIU-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-hydroxy-2-phenylacetate Chemical compound OCCOCCOC(=O)C(O)C1=CC=CC=C1 YWEJNVNVJGORIU-UHFFFAOYSA-N 0.000 description 2
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 2
- UPFQJMVQJWHPOL-UHFFFAOYSA-N 2-methyl-1-phenylpropane-1,2-diol Chemical compound CC(C)(O)C(O)C1=CC=CC=C1 UPFQJMVQJWHPOL-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 2
- YJVIKVWFGPLAFS-UHFFFAOYSA-N 9-(2-methylprop-2-enoyloxy)nonyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCOC(=O)C(C)=C YJVIKVWFGPLAFS-UHFFFAOYSA-N 0.000 description 2
- PGDIJTMOHORACQ-UHFFFAOYSA-N 9-prop-2-enoyloxynonyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCOC(=O)C=C PGDIJTMOHORACQ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical group CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 238000009832 plasma treatment Methods 0.000 description 2
- 229920005650 polypropylene glycol diacrylate Polymers 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- MAPRVCYXNJMHGD-UHFFFAOYSA-N (2-benzoyl-3,4,5-trimethylphenyl)-phenylphosphinic acid Chemical class CC=1C(=C(C(=C(C1)P(O)(=O)C1=CC=CC=C1)C(C1=CC=CC=C1)=O)C)C MAPRVCYXNJMHGD-UHFFFAOYSA-N 0.000 description 1
- VTESCYNPUGSWKG-UHFFFAOYSA-N (4-tert-butylphenyl)hydrazine;hydrochloride Chemical compound [Cl-].CC(C)(C)C1=CC=C(N[NH3+])C=C1 VTESCYNPUGSWKG-UHFFFAOYSA-N 0.000 description 1
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- GZZRDBYXGPSMCR-UHFFFAOYSA-N 1-(2-chlorophenyl)-3,5-bis(trichloromethyl)-1,3,5-triazinane Chemical compound ClC1=CC=CC=C1N1CN(C(Cl)(Cl)Cl)CN(C(Cl)(Cl)Cl)C1 GZZRDBYXGPSMCR-UHFFFAOYSA-N 0.000 description 1
- YQBKVGJYMFZJRZ-UHFFFAOYSA-N 1-(9h-carbazol-3-yl)-2-(dimethylamino)-2-methylpropan-1-one Chemical compound C1=CC=C2C3=CC(C(=O)C(C)(C)N(C)C)=CC=C3NC2=C1 YQBKVGJYMFZJRZ-UHFFFAOYSA-N 0.000 description 1
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- RWEAGLZFYKQPLZ-UHFFFAOYSA-N 1-[4,5-diphenyl-2-(2,4,6-trichlorophenyl)imidazol-2-yl]-4,5-diphenyl-2-(2,4,6-trichlorophenyl)imidazole Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C(N1C2(N=C(C(=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C(=CC(Cl)=CC=2Cl)Cl)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 RWEAGLZFYKQPLZ-UHFFFAOYSA-N 0.000 description 1
- XKMMRDFNYVHBLL-UHFFFAOYSA-N 1-[4-[[4-(1,2-dihydroxy-2-methylpropyl)phenyl]methyl]phenyl]-2-hydroxy-2-methylpropan-1-one Chemical compound C1=CC(C(O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 XKMMRDFNYVHBLL-UHFFFAOYSA-N 0.000 description 1
- HGQRQJQLAONGAJ-UHFFFAOYSA-N 1-[9-dodecyl-6-(2-methyl-2-morpholin-4-ylpropanoyl)carbazol-3-yl]-2-methyl-2-morpholin-4-ylpropan-1-one Chemical compound C=1C=C2N(CCCCCCCCCCCC)C3=CC=C(C(=O)C(C)(C)N4CCOCC4)C=C3C2=CC=1C(=O)C(C)(C)N1CCOCC1 HGQRQJQLAONGAJ-UHFFFAOYSA-N 0.000 description 1
- BOXFZQOSJPDVOZ-UHFFFAOYSA-N 1-propan-2-ylxanthen-9-one Chemical compound O1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C BOXFZQOSJPDVOZ-UHFFFAOYSA-N 0.000 description 1
- LRZPQLZONWIQOJ-UHFFFAOYSA-N 10-(2-methylprop-2-enoyloxy)decyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCOC(=O)C(C)=C LRZPQLZONWIQOJ-UHFFFAOYSA-N 0.000 description 1
- RHNJVKIVSXGYBD-UHFFFAOYSA-N 10-prop-2-enoyloxydecyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCCOC(=O)C=C RHNJVKIVSXGYBD-UHFFFAOYSA-N 0.000 description 1
- YIYBRXKMQFDHSM-UHFFFAOYSA-N 2,2'-Dihydroxybenzophenone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1O YIYBRXKMQFDHSM-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- IETCLBGYEVVQQL-UHFFFAOYSA-N 2-(2,4-dibromophenyl)-1-[2-(2,4-dibromophenyl)-4,5-diphenylimidazol-2-yl]-4,5-diphenylimidazole Chemical compound BrC1=CC(Br)=CC=C1C(N1C2(N=C(C(=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C(=CC(Br)=CC=2)Br)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 IETCLBGYEVVQQL-UHFFFAOYSA-N 0.000 description 1
- JKQRNTIBBOTABS-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-[2-(2,4-dichlorophenyl)-4,5-diphenylimidazol-2-yl]-4,5-diphenylimidazole Chemical compound ClC1=CC(Cl)=CC=C1C(N1C2(N=C(C(=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JKQRNTIBBOTABS-UHFFFAOYSA-N 0.000 description 1
- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 1
- FIOCEWASVZHBTK-UHFFFAOYSA-N 2-[2-(2-oxo-2-phenylacetyl)oxyethoxy]ethyl 2-oxo-2-phenylacetate Chemical compound C=1C=CC=CC=1C(=O)C(=O)OCCOCCOC(=O)C(=O)C1=CC=CC=C1 FIOCEWASVZHBTK-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- NACPTFCBIGBTSJ-UHFFFAOYSA-N 2-hydroxy-2-phenyl-1-(2-propan-2-ylphenyl)ethanone Chemical compound CC(C)C1=CC=CC=C1C(=O)C(O)C1=CC=CC=C1 NACPTFCBIGBTSJ-UHFFFAOYSA-N 0.000 description 1
- XBGVQVDENOPZGD-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-ol Chemical compound C1=CC(SC)=CC=C1C(O)C(C)(C)N1CCOCC1 XBGVQVDENOPZGD-UHFFFAOYSA-N 0.000 description 1
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 1
- MVMOMSLTZMMLJR-UHFFFAOYSA-N 4-[2-(1,3-benzothiazol-2-yl)ethenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C=CC1=NC2=CC=CC=C2S1 MVMOMSLTZMMLJR-UHFFFAOYSA-N 0.000 description 1
- DQOPDYYQICTYEY-UHFFFAOYSA-N 4-[2-(1,3-benzoxazol-2-yl)ethenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C=CC1=NC2=CC=CC=C2O1 DQOPDYYQICTYEY-UHFFFAOYSA-N 0.000 description 1
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- LOCXTTRLSIDGPS-FVDSYPCUSA-N [(z)-[1-oxo-1-(4-phenylsulfanylphenyl)octan-2-ylidene]amino] benzoate Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1C(=O)C(/CCCCCC)=N\OC(=O)C1=CC=CC=C1 LOCXTTRLSIDGPS-FVDSYPCUSA-N 0.000 description 1
- ULQMPOIOSDXIGC-UHFFFAOYSA-N [2,2-dimethyl-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)COC(=O)C(C)=C ULQMPOIOSDXIGC-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001924 cycloalkanes Chemical group 0.000 description 1
- 150000001925 cycloalkenes Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- KGGOIDKBHYYNIC-UHFFFAOYSA-N ditert-butyl 4-[3,4-bis(tert-butylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=C1 KGGOIDKBHYYNIC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- LJUJMKJGPIXNAK-UHFFFAOYSA-N ethyl 4-[2-(2-chlorophenyl)-1-[2-(2-chlorophenyl)-4,5-bis(4-ethoxycarbonylphenyl)imidazol-2-yl]-5-(4-ethoxycarbonylphenyl)imidazol-4-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1=NC(N2C(=C(N=C2C=2C(=CC=CC=2)Cl)C=2C=CC(=CC=2)C(=O)OCC)C=2C=CC(=CC=2)C(=O)OCC)(C=2C(=CC=CC=2)Cl)N=C1C1=CC=C(C(=O)OCC)C=C1 LJUJMKJGPIXNAK-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001552 radio frequency sputter deposition Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/80—Constructional details
- H10K59/87—Passivation; Containers; Encapsulations
- H10K59/871—Self-supporting sealing arrangements
- H10K59/8722—Peripheral sealing arrangements, e.g. adhesives, sealants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/844—Encapsulations
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/02—Details
- H05B33/04—Sealing arrangements, e.g. against humidity
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/80—Constructional details
- H10K59/87—Passivation; Containers; Encapsulations
- H10K59/873—Encapsulations
Definitions
- the present invention relates to a sealant for a display element, a cured product thereof, and a display device.
- Organic EL elements are being used in displays, lighting devices, and the like because they consume less power. Since organic EL elements are easily deteriorated by moisture and oxygen in the atmosphere, they are used by being sealed with various sealing members, and the durability of moisture and oxygen of various sealing members will be improved for practical use. It is desired.
- a method for sealing the organic EL for example, a method is used in which a resin layer is formed on an organic EL element coated with a first layer of an inorganic material film, and then a second layer of the inorganic material film is coated. ing.
- the method of coating with the inorganic material film include a method of forming an inorganic material film made of silicon nitride or silicon oxide by a sputtering method, an electron cyclotron resonance (ECR) plasma CVD method, or the like.
- ECR electron cyclotron resonance
- the encapsulant for an organic electroluminescence display element includes an acyclic alkanediol di (meth) acrylate having 6 or more carbon atoms, and a cyclic monofunctional (meth) acrylate and a cyclic bifunctional (meth) acrylate. It is described that it is used in combination with a cyclic monomer containing. According to the same document, it is said that a sealing agent having excellent ejection properties when using an inkjet and having excellent reliability of the obtained organic EL element can be obtained.
- the present invention provides a sealant for a display element, which has excellent plasma resistance and has both a viscosity and a low dielectric constant that can be stably applied by an inkjet method.
- a sealant for a display element containing a polymerizable compound and a curing agent contains the following components (A) and (B): (A) (meth) acrylate having a bifunctional or higher alicyclic structure (B) containing (meth) acrylate having a bifunctional chain structure.
- the content of the component (A) is 60 parts by mass or less with respect to a total of 100 parts by mass of the components (A) and (B).
- Component (C) in the sealant for a display element A sealant for a display element, wherein the content of the monofunctional (meth) acrylate is 1 part by mass or less with respect to 100 parts by mass of the polymerizable compound.
- the component (B) is 1,12-dodecanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, triethylene glycol di (meth) acrylate and tripropylene glycol di (meth).
- a sealing agent for a display element which is excellent in plasma resistance and has both a viscosity and a low dielectric constant that can be stably applied by an inkjet method.
- the sealing agent for a display element (hereinafter, also simply referred to as “sealing agent” as appropriate) is a composition used for sealing an element, and contains a polymerizable compound and a curing agent.
- the polymerizable compound has the following components (A) and (B): (A) (Meta) acrylate having a bifunctional or higher alicyclic structure (B) Containing (meth) acrylate having a bifunctional chain structure, with respect to a total of 100 parts by mass of the components (A) and (B).
- the content of the component (A) is 60 parts by mass or less.
- the content of the component (C): monofunctional (meth) acrylate in the sealant for a display device is 1 part by mass or less with respect to 100 parts by mass of the polymerizable compound.
- (meth) acrylate means at least one of acrylate and methacrylate.
- (meth) acrylic means at least one of acrylic and methacrylic.
- the polymerizable compound may be any compound having a polymerizable functional group, and is preferably a compound having a radically polymerizable functional group.
- the polymerizable compound contains the above-mentioned components (A) and (B).
- the component (A) is a (meth) acrylate having a bifunctional or higher alicyclic structure.
- the component (A) is a (meth) acrylate having an alicyclic structure in the molecular structure and two or more (meth) acrylic groups, and is preferably (meth) from the viewpoint of improving strength. It is a (meth) acrylate having two acrylic groups.
- the component (A) has an alicyclic hydrocarbon structure in the molecular structure, and the number of carbon atoms in the alicyclic hydrocarbon structure is preferably 4 or more from the viewpoint of improving heat resistance. It is more preferably 5 or more, still more preferably 6 or more, preferably 14 or less, still more preferably 12 or less, still more preferably 10 or less.
- the alicyclic hydrocarbon structure may be a saturated hydrocarbon structure or an unsaturated hydrocarbon structure. From the viewpoint of improving heat resistance, the alicyclic hydrocarbon structure is preferably a saturated hydrocarbon structure.
- the alicyclic hydrocarbon structure may be a monocyclic hydrocarbon structure, a fused ring hydrocarbon structure, or a polycyclic hydrocarbon structure having a bridge ring hydrocarbon group structure.
- the component (A) may contain a group containing these alicyclic hydrocarbon structures in the molecular structure, and preferably contains a divalent group containing the alicyclic hydrocarbon structure.
- Specific examples of the monocyclic hydrocarbon group include a group having a cycloalkane structure such as a cyclohexylene group and a cyclohexyl group; and a group having a cycloalkene skeleton such as a cyclodecatoriendiyl group and a cyclodecatorien group.
- polycyclic hydrocarbon group examples include a group having a dicyclopentadiene skeleton such as a tricyclodecandyl group, a dicyclopentanyl group, and a dicyclopentenyl group; a norbornanediyl group, an isobornandyl group, and a norbornyl group.
- Groups having a norbornane skeleton such as an isobornyl group; groups having an adamantane skeleton such as an adamantane diyl group and an adamantane group can be mentioned.
- the cyclic hydrocarbon group in the component (A) is preferably a group having a dicyclopentadiene skeleton from the viewpoint of improving plasma resistance and low moisture permeability. Further, the component (A) contains tricyclodecanedimethanol di (meth) acrylate from the viewpoint of improving plasma resistance and low moisture permeability, and is more preferably tricyclodecanedimethanol di (meth) acrylate. ..
- the content of the component (A) in the encapsulant is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, still more preferably 10 parts by mass or more with respect to 100 parts by mass of the polymerizable compound from the viewpoint of improving heat resistance. It is 15 parts by mass or more, more preferably 20 parts by mass or more, and even more preferably 25 parts by mass or more. Further, from the viewpoint of making the inkjet coatability more preferable, the content of the component (A) in the encapsulant is preferably 60 parts by mass or less, more preferably 58 with respect to 100 parts by mass of the polymerizable compound. It is not more than parts by mass, more preferably 56 parts by mass or less.
- the component (B) is a (meth) acrylate having a bifunctional chain structure.
- the component (B) is a (meth) acrylate having a chain structure in the molecular structure and two or more (meth) acrylic groups, and is preferably (meth) from the viewpoint of improving strength. It is a (meth) acrylate having two acrylic groups.
- Specific examples of the component (B) include di (meth) acrylate of alkanediol and di (meth) acrylate of (poly) alkylene glycol.
- the chain structure may be a linear structure or a structure having branches.
- the chain structure preferably contains a divalent hydrocarbon group having a straight chain or a branched chain from the viewpoint of making the inkjet coatability more preferable.
- the number of carbon atoms of the divalent hydrocarbon group is, for example, 1 or more, preferably 2 or more, and more preferably 4 or more, from the viewpoint of accessibility of the monomer. Further, from the viewpoint of improving heat resistance, the number of carbon atoms of the divalent hydrocarbon group is preferably 20 or less, more preferably 14 or less.
- 1,6-hexanediol diacrylate for example, A-HD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
- 1,9-nonanediol diacrylate for example, A-NOD-
- Polypropylene glycol diacrylate eg A-400, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
- Polypropylene glycol diacrylate eg APG-400, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
- Tripropylene glycol diacrylate eg SR306H, Alchema
- 1,3-Butanediol dimethacrylate eg BG, manufactured by Shin-Nakamura Chemical Industry
- 1,4-butanediol dimethacrylate eg BD, manufactured by Shin-Nakamura Chemical Industry
- 1,6-hexanediol Dimethacrylate eg HD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
- 1,9-Nonandiol dimethacrylate eg NOD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd .
- Light acrylate 1,9-ND-M manufactured by Kyoeisha Chemical
- the component (B) is 1,12-dodecanediol di (meth) acrylate and 1,9-nonanediol.
- One or more (meth) acrylates selected from the group consisting of di (meth) acrylates, triethylene glycol di (meth) acrylates and tripropylene glycol di (meth) acrylates.
- the content of the component (B) in the encapsulant is preferably 5 parts by mass or more, and more preferably 10 parts by mass with respect to 100 parts by mass of the polymerizable compound from the viewpoint of making the inkjet coatability more preferable.
- the above is more preferably 15 parts by mass or more, further preferably 20 parts by mass or more, still more preferably 25 parts by mass or more, and further preferably 40 parts by mass or more.
- the content of the component (B) in the encapsulant is, for example, 75 parts by mass or less, preferably 60 parts by mass or less, based on 100 parts by mass of the polymerizable compound. It is more preferably 58 parts by mass or less, still more preferably 56 parts by mass or less.
- the content of the component (A) with respect to a total of 100 parts by mass of the components (A) and (B) is 60 parts by mass or less, preferably 58 parts by mass or less, from the viewpoint of making the inkjet coatability more preferable. , More preferably 55 parts by mass or less, still more preferably 50 parts by mass or less.
- the lower limit of the content of the component (A) with respect to a total of 100 parts by mass of the components (A) and (B) is more than 0 parts by mass, preferably 10 parts by mass or more from the viewpoint of improving plasma resistance. It is more preferably 15 parts by mass or more, further preferably 20 parts by mass or more, still more preferably 25 parts by mass or more, still more preferably 30 parts by mass or more, still more preferably 40 parts by mass or more.
- the component (C) is a monofunctional (meth) acrylate.
- Specific examples of the component (C) include mono (meth) acrylate having a hydrocarbon group having a linear or branched chain in the molecular structure, and mono (meth) acrylate having an aromatic hydrocarbon group in the molecular structure. ..
- An example of the former is lauryl methacrylate, and an example of the latter is 3-phenoxybenzyl acrylate.
- the sealant for a display element preferably does not contain the component (C). That is, the content of the component (C) in the sealant for a display device is preferably 0 parts by mass with respect to 100 parts by mass of the polymerizable compound.
- the content of the component (C) in the sealant for display elements exceeds 0 parts by mass with respect to 100 parts by mass of the polymerizable compound. It is 1 part by mass or less, preferably 0.5 part by mass or less, more preferably 0.1 part by mass or less, and further preferably 0.01 part by mass or less.
- the content of the polymerizable compound in the sealant for a display element is preferably 70% by mass or more, more preferably 80% by mass, based on the total composition of the sealant from the viewpoint of improving the strength of the cured product. As mentioned above, it is more preferably 85% by mass or more, still more preferably 90% by mass or more, and even more preferably 93% by mass or more. Further, from the viewpoint of improving the weather resistance of the encapsulant, the content of the polymerizable compound in the encapsulant is preferably 99.9% by mass or less, more preferably 99.9% by mass or less, based on the total composition of the encapsulant. It is 99.5% by mass or less, more preferably 99% by mass or less, and even more preferably 98% by mass or less.
- the curing agent include a polymerization initiator.
- the polymerization initiator is preferably a photopolymerization initiator which is a compound that generates radicals or acids by irradiation with ultraviolet rays or visible light from the viewpoint of stably forming a cured product at a low temperature.
- the photopolymerization initiator include an acylphosphine oxide-based initiator, an oxyphenylacetic acid ester-based initiator, a benzoylformic acid-based initiator, a hydroxyphenylketone-based initiator, and the like.
- photopolymerization initiator examples include benzophenone, Michler's ketone, 4,4'-bis (diethylamino) benzophenone, xanthone, thioxanthone, isopropylxanthone, 2,4-diethylthioxanthone, 2-ethylanthraquinone, acetophenone, and 2-hydroxy-.
- the photopolymerization initiator is preferably 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-phenyl-1-propanol, 1- [4- ( 2-Hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propanone, 2-hydroxy-1- ⁇ 4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] phenyl ⁇ - 2-Methyl-1-propanol, 2,2-dimethoxy-2-phenylacetophenone, oxy-phenyl-acetic acid 2- [2-oxo-2-phenyl-acetoxy-ethoxy] -ethyl ester, oxy-phenyl-acetic acid 2- [2-Hydroxy-ethoxy] -ethyl ester, methyl benzoylate, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, 2,4,6-
- Irgacure184 As commercial products of the photopolymerization initiator, Irgacure184, Irgacure651, Irgacure127, Irgacure1173, Irgacure500, Irgacure2959, Irgacure754, IrgacureMBF, IrgacureMBF, IrgacureMBF, IrgacureTPO (above, BASF), etc.
- the content of the polymerization initiator in the encapsulant is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, based on the total composition of the encapsulant, from the viewpoint of improving the curability. , More preferably 1% by mass or more, still more preferably 2% by mass or more. Further, from the viewpoint of suppressing the coloring of the encapsulant, the content of the polymerization initiator in the encapsulant is preferably 10% by mass or less, more preferably 8% by mass, based on the total composition of the encapsulant. Below, it is more preferably 7% by mass or less, still more preferably 6% by mass or less, and even more preferably 5% by mass or less.
- the encapsulant may be composed of a polymerizable compound and a curing agent, or may contain components other than these. Specific examples of other components include tackifiers, fillers, curing accelerators, plasticizers, surfactants, heat stabilizers, flame retardants, antistatic agents, defoamers, leveling agents and UV absorbers. 1 or 2 or more additives selected from.
- the glass transition temperature (Tg) of the cured product of the encapsulant is 50 ° C. or higher, preferably 60 ° C. or higher, and more preferably 70 ° C. or higher from the viewpoint of improving the heat resistance of the encapsulant. Further, from the viewpoint of improving the flexibility, the Tg of the cured product of the encapsulant is less than 200 ° C., preferably 190 ° C. or lower, more preferably 180 ° C. or lower.
- the Tg of the encapsulant is specifically measured by the following method.
- a 100 ⁇ m-thick Teflon (registered trademark) sheet is used as a mold, an uncured encapsulant is sandwiched between PET films, and an illuminance of 1000 mW / cm 2 is used with a UV-LED having a wavelength of 395 nm. It is obtained by curing under the condition of an integrated light amount of 1500 mJ / cm 2 .
- the obtained cured product is cut into a size of 10 mm in width ⁇ 40 mm in length with a cutter to obtain a measurement sample.
- the Tg of the cured product is heated from room temperature to 250 ° C.
- the properties of the encapsulant are not limited, and the encapsulant is suitable from the viewpoint of improving the flexibility and plasma resistance of the encapsulating material and being suitable for forming a cured material by a coating method such as an inkjet method. It is preferably liquid.
- the sealing agent is preferably a sealing agent used for coating, and more preferably a sealing used for coating by an inkjet method. It is a stop agent.
- the viscosity of the encapsulant measured at 25 ° C. and 20 rpm using an E-type viscometer is preferably 5 mPa ⁇ s or more, more preferably 8 mPa ⁇ s or more, still more preferably, from the viewpoint of improving the inkjet ejection property. Is 10 mPa ⁇ s or more. Further, from the viewpoint of improving the inkjet ejection property, the viscosity of the encapsulant is preferably 30 mPa ⁇ s or less, more preferably less than 30.0 mPa ⁇ s, still more preferably 28.5 mPa ⁇ s or less, still more preferably. Is 27 mPa ⁇ s or less.
- the dielectric constant of the cured product of the sealant is preferably less than 3.5, more preferably 3.4 or less, still more preferably 3.3 or less, and further, from the viewpoint of improving the sealing characteristics of the sealant. It is more preferably 3.2 or less, and even more preferably 3.1 or less. Further, the dielectric constant of the cured product of the encapsulant can be, for example, 1.0 or more.
- the dielectric constant of the cured product of the encapsulant is the cured product obtained by curing the curable composition under the conditions of an illuminance of 1000 mW / cm 2 and an integrated light intensity of 1500 mJ / cm 2 with a UV-LED having a wavelength of 395 nm. Permittivity measured at a frequency of 100 kHz.
- the method for producing the encapsulant is not limited, and includes, for example, mixing a polymerizable compound, a curing agent, and other components as appropriate, for example, various additives to be added as needed.
- various known kneaders such as a planetary stirrer, a homodisper, a universal mixer, a Banbury mixer, a kneader, two rolls, three rolls, and an extruder are used alone or in combination. Examples thereof include a method of uniformly kneading under conditions such as normal pressure, reduced pressure, pressure, and an inert gas stream under normal temperature or heating.
- a sealing material can be formed by using the obtained sealing agent.
- a sealant may be applied onto the substrate and dried.
- a known method such as an inkjet method, screen printing, or dispenser coating can be used. Further, the drying can be performed, for example, by heating to a temperature at which the polymerizable compound does not polymerize.
- the shape of the obtained encapsulating material is not limited and may be, for example, a film or a layer.
- the encapsulating material is, for example, a cured product obtained by curing the encapsulant in the present embodiment, and more specifically, a photocured product of the encapsulant.
- methods for photocuring the encapsulant include low-pressure mercury lamps, medium-pressure mercury lamps, high-pressure mercury lamps, ultra-high pressure mercury lamps, excima lasers, chemical lamps, black light lamps, microwave-excited mercury lamps, metal halide lamps, sodium lamps, and halogen lamps.
- a method of curing by irradiating light using a light source such as a xenon lamp, an LED lamp, a fluorescent lamp, sunlight, or an electron beam irradiator.
- the polymerizable compound contains the components (A) and (B) in a specific ratio and the content when the component (C) is contained is in a specific range, such a polymerizable compound and curing
- a sealing agent containing an agent it is possible to obtain a sealing material having excellent plasma resistance and having both a viscosity and a low dielectric constant that can be stably applied by an inkjet method.
- the resin layer obtained from such a polymerizable compound as a sealing material for example, it is possible to obtain a display device having excellent reliability.
- the encapsulant obtained in the present embodiment is suitably used for encapsulating a display element, preferably an organic EL display element, for example.
- a sealing agent having excellent plasma resistance being able to be stably applied by an inkjet method when forming a resin layer, and having an effectively reduced dielectric constant. Therefore, for example, damage to the display element in the manufacturing process of the display device can be effectively suppressed, and the manufacturing stability of the display device can be improved.
- a configuration example of the display device will be given by taking an organic EL display device as an example.
- the organic EL display device has a layer made of a cured product of a sealing agent.
- the organic EL display device may have a top emission structure or a bottom emission structure.
- the organic EL element is arranged on a substrate and is pre-coated with an inorganic material film so as to cover the region containing the organic EL element before being protected by the resin layer obtained by curing the encapsulant in the present embodiment. It is preferable that it is.
- FIG. 1 is a cross-sectional view showing a configuration example of an organic EL display device according to the present embodiment.
- the display device 100 shown in FIG. 1 is an organic EL display device, and covers a substrate (base material layer 50), a display element (light emitting element 10) arranged on the base material layer 50, and a light emitting element 10.
- the sealing layer 22 (which may be the overcoat layer 22 or the barrier layer 22) is included. Then, for example, the sealing layer 22 is composed of a cured product of the sealing agent in the present embodiment.
- the light emitting element 10 is an organic EL display element. Further, in FIG.
- the display device 100 has a barrier layer 21 (may be a touch panel layer 21 or a surface protection layer 21) and a sealing layer 22 (which may be a touch panel layer 21 or a surface protection layer 21) as layers located on the observation side of the light emitting element 10. It has an overcoat layer 22 or a barrier layer 22), a flattening layer 23 (may be a sealing layer 23), and a barrier layer 24.
- the flattening layer 23 is provided on the base material layer 50 so as to cover the light emitting element 10, and the barrier layer 24 is provided on the surface of the flattening layer 23.
- the sealing layer 22 is provided on the base material layer 50 so as to cover the flattening layer 23 and the barrier layer 24. Further, a barrier layer 21 is provided on the sealing layer 22.
- the material of the base material layer 50 is not limited, and various materials such as a glass substrate, a silicon substrate, and a plastic substrate can be used.
- a TFT substrate having a plurality of TFTs (thin film transistors) and a flattening layer on the substrate can also be used.
- Examples of the inorganic material constituting the barrier layer 24, that is, the above-mentioned inorganic material film, include silicon nitride (SiN x ), silicon oxide (SiO x ), aluminum oxide (Al 2 O 3 ), and the like.
- the inorganic material film may be a single layer or a laminated body of a plurality of types of layers.
- Examples of the method of covering the light emitting element 10 with the inorganic material film include a sputtering method and an electron cyclotron resonance (ECR) plasma CVD method when the inorganic material film is made of silicon nitride or silicon oxide.
- ECR electron cyclotron resonance
- the sputtering method can be carried out under the conditions of room temperature, electric power of 50 to 1000 W, and pressure of 0.001 to 0.1 Torr, for example, using a single gas such as argon or nitrogen as a carrier gas or a mixed gas.
- a mixed gas of SiH 4 and O 2 or a mixed gas of SiH 4 and N 2 is used, and the temperature is 30 ° C to 100 ° C, the pressure is 10 mTorr to 1Torr, the frequency is 2.45 GHz, and the power is increased. It can be performed under the condition of 10 to 1000 W.
- the thickness of the inorganic material film formed on the light emitting device 10 is not limited, but is, for example, 0.01 to 10 ⁇ m, preferably 0.1 to 5 ⁇ m from the viewpoint of improving the sealing performance and the flexible performance. ..
- a sealing layer 22 for example, a method of applying a sealing agent on the light emitting element 10 and curing the light emitting element 10. And so on.
- a coating method it is preferable to use an inkjet method.
- the thickness of the resin layer is not limited, but is, for example, 0.1 to 50 ⁇ m, preferably 1 to 20 ⁇ m from the viewpoint of improving the sealing performance and the flexible performance.
- an inorganic material film (barrier layer 24) on the above-mentioned resin layer.
- the inorganic material and the forming method for forming the inorganic material film laminated on the resin layer are the same as those for the inorganic material film covering the light emitting element 10 described above.
- the thickness of the inorganic material film formed on the resin layer is not limited, but is, for example, 0.01 to 10 ⁇ m, preferably 0.1 to 5 ⁇ m from the viewpoint of improving the sealing performance and the flexible performance.
- the barrier layer 24 and the sealing layer 22 are provided on the light emitting element 10, and the sealing layer 22 is composed of a resin layer obtained by curing the sealing agent in the present embodiment. Therefore, it is possible to obtain a display device 100 having excellent reliability. Specifically, damage to the barrier layer 24 can be suppressed even when the plasma treatment step is performed when the barrier layer 24 is formed on the sealing layer 22. Further, for example, it is possible to suppress the generation of pinholes in the barrier layer 24 which is a SiN x film.
- (Polymerizable compound) (A) Alicyclic UV curable resin 1: Dimethylol-tricyclodecanediacrylate, light acrylate DCP-A, UV curable resin manufactured by Kyoeisha Chemical Co., Ltd .2: Dimethylol-tricyclodecanedimethacrylate, light acrylate DCP-M, Kyoeisha Chemical Co., Ltd. (B) Chain UV curable resin 3: 1,12-dodecanediol dimethacrylate, SR262, Alchema UV curable resin 4: 1,9-nonanediol diacrylate, light acrylate 1,9ND-A, Kyoeisha Chemical Co., Ltd.
- UV curable resin 5 1,9-nonanediol dimethacrylate, light acrylate 1,9ND-M
- UV curable resin 6 Triethylene glycol diacrylate, SR272
- UV curable resin 7 Tri Propropylene glycol diacrylate, SR306H, manufactured by Alchema
- (C) -1 Linear monofunctional UV curable resin 8: Lauryl methacrylate, light acrylate L, manufactured by Kyoeisha Chemical Co., Ltd.
- (C) -2 Aromatic monofunctional UV curable resin 9: 3-phenoxybenzyl acrylate, light acrylate POB -A, manufactured by Kyoeisha Chemical Co., Ltd.
- UV Radical Initiator 1 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, Omnirad TPO H, manufactured by IGM Resins
- Example 1 Example 1 to 5, Comparative Examples 1 to 4
- Each component was blended so as to have the blending composition shown in Table 1 to obtain a liquid curable composition as a sealing agent.
- the characteristics of the encapsulant or the cured product thereof obtained in each example were measured by the following methods. The measurement results are also shown in Table 1.
- viscosity The viscosity of the curable composition obtained in each example was measured at 25 ° C. and 20 rpm using an E-type viscometer (LV DV-II + Pro, manufactured by BROOKFIELD). Those having a measured viscosity of less than 30 mPa ⁇ s were regarded as acceptable.
- a cured product of the encapsulant was obtained by the following procedure. That is, using a 100 ⁇ m thick Teflon (registered trademark) sheet as a mold, an uncured encapsulant is sandwiched between PET films, and a UV-LED with a wavelength of 395 nm has an illuminance of 1000 mW / cm 2 and an integrated light intensity of 1500 mJ / cm 2 . It was cured under the conditions to obtain a cured product. The obtained cured product was cut into a size of 10 mm in width ⁇ 40 mm in length with a cutter to obtain a measurement sample.
- Teflon registered trademark
- the tan ⁇ was measured by the dynamic viscoelasticity measuring device “DMS6100” while applying a frequency of 1 Hz to the measured sample of the cured product in the atmosphere and raising the temperature from room temperature to 250 ° C. at 5 ° C./min.
- the temperature of the peak top of the obtained tan ⁇ was defined as Tg.
- a coating film for obtaining a cured product for measuring the dielectric constant was prepared by the following method. That is, the obtained encapsulant was introduced into an inkjet cartridge DMC-11610 (manufactured by FUJIFILM Dimension). The inkjet cartridge was set in an inkjet device DMP-2831 (manufactured by Fujifilm Dimatix), and after adjusting the ejection state, the thickness after curing was increased on a substrate on which aluminum was vapor-deposited to a thickness of 100 nm on non-alkali glass. It was applied in a size of 5 cm ⁇ 5 cm so as to be 10 ⁇ m.
- the obtained coating film was placed in a box at room temperature (25 ° C.) for 5 minutes to allow nitrogen to flow, and then irradiated with ultraviolet rays having a wavelength of 395 nm under the conditions of an illuminance of 1000 mW / cm 2 and an integrated light intensity of 1500 mJ / cm 2 , and cured. A film was formed. Then, aluminum was deposited on the inkjet coated surface to a thickness of 100 nm, and the dielectric constant was measured with an LCR meter HP4284A (manufactured by Agilent Technologies) under the condition of 100 kHz by an automatic balanced bridge method. Those with a measured dielectric constant of less than 3.5 were considered acceptable.
- the encapsulant obtained in each example was introduced into an inkjet cartridge DMC-11610 (manufactured by FUJIFILM Dimension).
- the inkjet cartridge is set in the inkjet device DMP-2831 (manufactured by Fujifilm Dimatic), and after adjusting the ejection state, the glass substrate has a size of 15 mm ⁇ 15 mm so that the cured thickness is 10 ⁇ m. Applied.
- the obtained coating film was placed in a box at room temperature (25 ° C.) for 5 minutes to allow nitrogen to flow, and then irradiated with ultraviolet rays having a wavelength of 395 nm at 1500 mW / cm 2 for 1 second to form a cured film.
- the sample on which the cured film was formed was plasma-treated for 1 minute under a pressure condition of 2500 W ICP power supply, 300 W RF power supply, DC bias 200 V, argon (Ar) flow rate 50 sccm, and 10 mtorr. Then, an inorganic sealing layer (SiN x film) having a film thickness of 100 nm was formed by an RF sputtering method using a SiN x target. On the other hand, an OLED element was vapor-deposited on a facing substrate and bonded to a substrate on which an inorganic sealing layer was formed to obtain an evaluation sample.
- SiN x film SiN x film
- the reliability test of the samples obtained in each example was carried out under the condition of 85 ° C. Specifically, the emission area ratio (%) after storing the samples obtained in each example at 85 ° C. for 100 hours was determined by the following method. That is, the light emitting area was calculated in the initial state and after storage for 100 hours using Motic Images Plus software (manufactured by Shimadzu Rika Co., Ltd.), and the light emitting area ratio was obtained. Those having a light emitting area ratio of 50% or more were regarded as acceptable.
- the encapsulants obtained in each example were excellent in the effect of suppressing damage to the organic EL element against plasma irradiation.
- the sealant obtained in each example had an excellent balance of viscosity, dielectric constant and Tg characteristics.
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Theoretical Computer Science (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
有機EL素子は、消費電力が少ないことから、ディスプレイや照明装置などに用いられつつある。有機EL素子は、大気中の水分や酸素によって劣化しやすいことから、各種シール部材で封止されて使用されており、実用化に向けては各種シール部材の水分や酸素の耐久性の向上が望まれている。
さらに、上記特許文献に記載の技術について本発明らが検討したところ、特許文献1においては、硬化体のガラス転移温度が高いため、フレキシブル性が要求されるデバイスには適さない場合があると予想される点で、改善の余地があった。
[1] 重合性化合物および硬化剤を含有する表示素子用封止剤であって、
前記重合性化合物が、以下の成分(A)および(B):
(A)2官能以上の脂環構造を有する(メタ)アクリレート
(B)2官能の鎖状構造を有する(メタ)アクリレート
を含み、
前記成分(A)および(B)の合計100質量部に対して前記成分(A)の含有量が60質量部以下であり、
当該表示素子用封止剤中の成分(C):単官能の(メタ)アクリレートの含有量が、前記重合性化合物100質量部に対して1質量部以下である、表示素子用封止剤。
[2] 前記成分(A)が、ジメチロール-トリシクロデカンジ(メタ)アクリレートを含む、[1]に記載の表示素子用封止剤。
[3] 前記成分(B)が、1,12-ドデカンジオールジ(メタ)アクリレート、1,9-ノナンジオールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレートおよびトリプロピレングリコールジ(メタ)アクリレートからなる群から選択される1または2以上の(メタ)アクリレートである、[1]または[2]に記載の表示素子用封止剤。
[4] 有機EL表示素子の封止用である、[1]乃至[3]いずれか1項に記載の表示素子用封止剤。
[5] [1]乃至[4]いずれか1項に記載の表示素子用封止剤を硬化してなる硬化物。
[6] 基板と、
前記基板上に配置された表示素子と、
前記表示素子を被覆する封止層と、
を含み、
前記封止層が、[1]乃至[4]いずれか1項に記載の表示素子用封止剤の硬化物により構成されている、表示装置。
本実施形態において、表示素子用封止剤(以下、適宜単に「封止剤」とも呼ぶ。)は、素子の封止に用いられる組成物であって、重合性化合物および硬化剤を含有する。重合性化合物は、以下の成分(A)および(B):
(A)2官能以上の脂環構造を有する(メタ)アクリレート
(B)2官能の鎖状構造を有する(メタ)アクリレート
を含み、成分(A)および(B)の合計100質量部に対して成分(A)の含有量が60質量部以下である。表示素子用封止剤中の成分(C):単官能の(メタ)アクリレートの含有量が、重合性化合物100質量部に対して1質量部以下である。
重合性化合物は、重合性の官能基を有する化合物であればよく、好ましくはラジカル重合性の官能基を有する化合物である。重合性化合物は、上述の成分(A)および(B)を含む。
成分(A)は、2官能以上の脂環構造を有する(メタ)アクリレートである。成分(A)は、具体的には、分子構造中に脂環構造を有するとともに、(メタ)アクリル基を2個以上有する(メタ)アクリレートであり、強度向上の観点から、好ましくは(メタ)アクリル基を2個有する(メタ)アクリレートである。
脂環式炭化水素構造は、飽和炭化水素構造であってよいし不飽和炭化水素構造であってもよい。耐熱性向上の観点から、脂環式炭化水素構造は、好ましくは飽和炭化水素構造である。
単環式炭化水素基の具体例として、シクロヘキシレン基、シクロヘキシル基等のシクロアルカン構造を有する基;シクロデカトリエンジイル基、シクロデカトリエン基等のシクロアルケン骨格を有する基が挙げられる。
多環式炭化水素基の具体例として、トリシクロデカンジイル基、ジシクロペンタニル基、ジシクロペンテニル基等のジシクロペンタジエン骨格を有する基;ノルボルナンジイル基、イソボルナンジイル基、ノルボルニル基、イソボルニル基等のノルボルナン骨格を有する基;アダマンタンジイル基、アダマンチル基等のアダマンタン骨格を有する基などが挙げられる。
また、成分(A)は、耐プラズマ性向上の観点および低透湿性の観点から、トリシクロデカンジメタノールジ(メタ)アクリレートを含み、より好ましくはトリシクロデカンジメタノールジ(メタ)アクリレートである。
また、インクジェット塗布性をより好ましいものとする観点から、封止剤中の成分(A)の含有量は、重合性化合物100質量部に対し、好ましくは60質量部以下であり、より好ましくは58質量部以下、さらに好ましくは56質量部以下である。
成分(B)は、2官能の鎖状構造を有する(メタ)アクリレートである。成分(B)は、具体的には、分子構造中に鎖状構造を有するとともに、(メタ)アクリル基を2個以上有する(メタ)アクリレートであり、強度向上の観点から、好ましくは(メタ)アクリル基を2個有する(メタ)アクリレートである。
成分(B)の具体例として、アルカンジオールのジ(メタ)アクリレート、(ポリ)アルキレングリコールのジ(メタ)アクリレートが挙げられる。
鎖状構造は、インクジェット塗布性をより好ましいものとする観点から、好ましくは直鎖または分岐鎖を有する2価の炭化水素基を含む。2価の炭化水素基の炭素数は、モノマー入手容易性の観点から、たとえば1以上であり、好ましくは2以上、より好ましくは4以上である。また、耐熱性向上の観点から、2価の炭化水素基の炭素数は、好ましくは20以下、より好ましくは14以下である。
また、耐プラズマ性向上の観点から、封止剤中の成分(B)の含有量は、重合性化合物100質量部に対し、たとえば75質量部以下であり、好ましくは60質量部以下であり、より好ましくは58質量部以下、さらに好ましくは56質量部以下である。
成分(A)および(B)の合計100質量部に対する成分(A)の含有量の下限値は、0質量部超であり、耐プラズマ性向上の観点から、好ましくは10質量部以上であり、より好ましくは15質量部以上、さらに好ましくは20質量部以上、さらにより好ましくは25質量部以上、よりいっそう好ましくは30質量部以上、さらにまた好ましくは40質量部以上である。
成分(C)は、単官能の(メタ)アクリレートである。成分(C)の具体例として、分子構造中に直鎖または分岐鎖を有する炭化水素基を有するモノ(メタ)アクリレート、分子構造中に芳香族炭化水素基を有するモノ(メタ)アクリレートが挙げられる。前者の例として、ラウリルメタクリレートが挙げられ、後者の例として、3-フェノキシベンジルアクリレートが挙げられる。
耐プラズマ性向上と耐熱性向上の観点から、表示素子用封止剤は好ましくは成分(C)を含まない。すなわち、表示素子用封止剤中の成分(C)の含有量は、重合性化合物100質量部に対して好ましくは0質量部である。
同様の観点から、表示素子用封止剤が成分(C)を含むとき、表示素子用封止剤中の成分(C)の含有量は、重合性化合物100質量部に対して0質量部超であり、また、1質量部以下であり、好ましくは0.5質量部以下、より好ましくは0.1質量部以下、さらに好ましくは0.01質量部以下である。
また、封止材料の耐候性を向上する観点から、封止剤中の重合性化合物の含有量は、封止剤の全組成に対し、好ましくは99.9質量%以下であり、より好ましくは99.5質量%以下、さらに好ましくは99質量%以下、よりいっそう好ましくは98質量%以下である。
硬化剤として、具体的には、重合開始剤が挙げられる。重合開始剤は、低温で安定的に硬化物を形成する観点から、好ましくは、紫外線または可視光線の照射によりラジカルまたは酸を発生する化合物である光重合開始剤である。光重合開始剤としては、アシルフォスフィンオキサイド系開始剤、オキシフェニル酢酸エステル系開始剤、ベンゾイルギ酸系開始剤およびヒドロキシフェニルケトン系開始剤等が挙げられる。
また、封止剤の着色を抑制する観点から、封止剤中の重合開始剤の含有量は、封止剤の全組成に対し、好ましくは10質量%以下であり、より好ましくは8質量%以下、さらに好ましくは7質量%以下、さらにより好ましくは6質量%以下、よりいっそう好ましくは5質量%以下である。
本実施形態において、封止剤は、重合性化合物および硬化剤から構成されてもよいし、これら以外の成分を含んでもよい。他の成分の具体例として、粘着付与剤、充填剤、硬化促進剤、可塑剤、界面活性剤、熱安定剤、難燃剤、帯電防止剤、消泡剤、レベリング剤および紫外線吸収剤からなる群から選択される1または2以上の添加剤が挙げられる。
封止剤の硬化物のガラス転移温度(Tg)は、封止材料の耐熱性向上の観点から、50℃以上であり、好ましくは60℃以上、より好ましくは70℃以上である。
また、屈曲性向上の観点から、封止剤の硬化物のTgは、200℃未満であり、好ましくは190℃以下、より好ましくは180℃以下である。
得られた硬化物をカッターで幅10mm×長さ40mmの大きさに切りだして測定試料を得る。
そして、硬化物のTgは、動的粘弾性測定装置「DMS6100」により、大気中にて硬化物の測定試料に1Hzの周波数をかけながら、室温から250℃まで5℃/分で昇温しながら、tanδを測定して、tanδのピークトップの温度をTgとする。
また、インクジェット吐出性向上の観点から、上記封止剤の粘度は、好ましくは30mPa・s以下であり、より好ましくは30.0mPa・s未満、さらに好ましくは28.5mPa・s以下、さらにより好ましくは27mPa・s以下である。
また、封止剤の硬化物の誘電率は、たとえば1.0以上とすることができる。
ここで、封止剤の硬化物の誘電率は、波長395nmのUV-LEDで照度1000mW/cm2、積算光量1500mJ/cm2の条件で硬化性組成物を硬化させて得られる硬化物について、周波数100kHzにて測定される誘電率である。
封止剤の製造方法は限定されず、たとえば、重合性化合物、硬化剤、および、適宜その他の成分、たとえば必要に応じて添加する各種添加剤を混合することを含む。各成分を混合する方法として、たとえば、遊星式撹拌装置、ホモディスパー、万能ミキサー、バンバリーミキサー、ニーダー、2本ロール、3本ロール、押出機等の公知の各種混練機を単独または併用して、常温下または加熱下で、常圧下、減圧下、加圧下または不活性ガス気流下等の条件下で均一に混練する方法が挙げられる。
封止剤を光硬化させる方法としては、たとえば、低圧水銀灯、中圧水銀灯、高圧水銀灯、超高圧水銀灯、エキシマレーザ、ケミカルランプ、ブラックライトランプ、マイクロウェーブ励起水銀灯、メタルハライドランプ、ナトリウムランプ、ハロゲンランプ、キセノンランプ、LEDランプ、蛍光灯、太陽光、電子線照射装置等の光源を使用して光照射して硬化させる方法が挙げられる。
以下、有機EL表示装置を例に、表示装置の構成例を挙げる。
本実施形態において、有機EL表示装置は、封止剤の硬化物により構成された層を有する。有機EL素子を、本実施形態の封止剤を硬化させて得られる樹脂層で保護することにより、有機EL素子内への水分の浸入を充分に防止して有機EL素子の性能および耐久性を高く維持することができる。
有機EL素子は、基板上に配置され、本実施形態における封止剤を硬化させて得られる樹脂層により保護される前に、上記有機EL素子を含む領域を覆うように予め無機材料膜で被覆されていることが好ましい。
また、図1においては、表示装置100が、発光素子10よりも観察側に位置する層として、バリア性層21(タッチパネル層21または表面保護層21であってもよい)、封止層22(オーバーコート層22またはバリア性層22であってもよい)、平坦化層23(封止層23であってもよい)、バリア性層24を有している。平坦化層23は、発光素子10を覆うように基材層50上に設けられており、バリア性層24は、平坦化層23の表面に設けられている。封止層22は、平坦化層23およびバリア性層24を覆うように基材層50上に設けられている。また、封止層22上にバリア性層21が設けられている。
無機材料膜によって発光素子10を被覆する方法は、たとえば上記無機材料膜が窒化珪素や酸化珪素からなる場合には、スパッタリング法や電子サイクロトロン共鳴(ECR)プラズマCVD法等が挙げられる。
また、ECRプラズマCVD法は、たとえば、SiH4とO2との混合ガス又はSiH4とN2との混合ガスを用い、温度30℃~100℃、圧力10mTorr~1Torr、周波数2.45GHz、電力10~1000Wの条件でおこなうことができる。
発光素子10の上に形成される無機材料膜の厚さは限定されないが、封止性能とフレキシブル性能を向上させる観点から、たとえば0.01~10μmであり、好ましくは0.1~5μmである。
樹脂層の厚さは限定されないが、封止性能とフレキシブル性能を向上させる観点から、たとえば0.1~50μmであり、好ましくは1~20μmである。
上記樹脂層上に形成される無機材料膜の厚さは限定されないが、封止性能とフレキシブル性能を向上させる観点から、たとえば0.01~10μmであり、好ましくは0.1~5μmである。
はじめに、以下の例において用いた材料を示す。
(A)脂環式
UV硬化樹脂1:ジメチロール-トリシクロデカンジアクリレート、ライトアクリレートDCP-A、共栄社化学社製
UV硬化樹脂2:ジメチロール-トリシクロデカンジメタクリレート、ライトアクリレートDCP-M、共栄社化学社製
(B)鎖状
UV硬化樹脂3:1,12-ドデカンジオールジメタクリレート、SR262、アルケマ社製
UV硬化樹脂4:1,9-ノナンジオールジアクリレート、ライトアクリレート1,9ND-A、共栄社化学社製
UV硬化樹脂5:1,9-ノナンジオールジメタクリレート、ライトアクリレート1,9ND-M、共栄社化学社製
UV硬化樹脂6:トリエチレングリコールジアクリレート、SR272、アルケマ社製
UV硬化樹脂7:トリプロピレングリコールジアクリレート、SR306H、アルケマ社製
UV硬化樹脂8:ラウリルメタクリレート、ライトアクリレートL、共栄社化学社製
(C)-2:芳香族単官能
UV硬化樹脂9:3-フェノキシベンジルアクリレート、ライトアクリレートPOB-A、共栄社化学社製
UVラジカル開始剤1:2,4,6-トリメチルベンゾイル-ジフェニルホスフィンオキサイド、Omnirad TPO H、IGM Resins社製
表1に示した配合組成となるように各成分を配合して、封止剤として液状の硬化性組成物を得た。
各例で得られた封止剤またはその硬化物の特性を以下の方法で測定した。測定結果を表1にあわせて示す。
各例で得られた硬化性組成物の粘度を、E型粘度計(LV DV-II+ Pro、BROOKFIELD社製)を用いて25℃、20rpmにて測定した。粘度の測定値が30mPa・s未満であるものを合格とした。
まず、以下の手順で封止剤の硬化物を得た。すなわち、100μm厚のテフロン(登録商標)シートを型枠として、PETフィルム間に未硬化の封止剤を挟みこみ、波長395nmのUV-LEDで照度1000mW/cm2、積算光量1500mJ/cm2の条件で硬化させ、硬化物を得た。
得られた硬化物をカッターで幅10mm×長さ40mmの大きさに切りだした、測定試料を得た。
そして、動的粘弾性測定装置「DMS6100」により、大気中にて硬化物の測定試料に1Hzの周波数をかけながら、室温から250℃まで5℃/分で昇温しながらtanδを測定した。得られたtanδのピークトップの温度をTgとした。
誘電率測定のための硬化物を得るための塗膜を以下の方法により作製した。すなわち、得られた封止剤を、インクジェットカートリッジDMC-11610(富士フイルムDimatix社製)に導入した。そのインクジェットカートリッジをインクジェット装置DMP-2831(富士フイルムDimatix社製)にセットし、吐出状態の調整を行った後、無アルカリガラス上にアルミニウムを100nmの厚みで蒸着した基板に、硬化後の厚みが10μmとなるように、5cm×5cmのサイズで塗布した。
得られた塗膜を5分間、室温(25℃)でボックスに入れて窒素をフローさせた後、波長395nmの紫外線を照度1000mW/cm2、積算光量1500mJ/cm2の条件で照射し、硬化膜を形成した。
その後、インクジェット塗布面にアルミニウムを100nmの厚みで蒸着し、LCRメーターHP4284A(アジレント・テクノロジー社製)にて、自動平衡ブリッジ法により条件100kHzにて誘電率を測定した。誘電率の測定値が3.5未満であるものを合格とした。
封止剤のプラズマ耐性の指標として、プラズマ処理工程における有機EL素子ダメージを以下の方法で評価した。
各例で得られた封止剤を、インクジェットカートリッジDMC-11610(富士フイルムDimatix社製)に導入した。そのインクジェットカートリッジをインクジェット装置DMP-2831(富士フイルムDimatix社製)にセットし、吐出状態の調整を行った後、ガラス基板に、硬化後の厚みが10μmとなるように、15mm×15mmのサイズで塗布した。
得られた塗膜を5分間、室温(25℃)でボックスに入れて窒素をフローさせた後、波長395nmの紫外線を1500mW/cm2で1秒間照射し、硬化膜を形成した。
その後、SiNxターゲットを用いてRFスパッタリング法により、膜厚100nmの無機封止層(SiNx膜)を形成した。
一方、対向基板にOLED素子を蒸着して、無機封止層が形成された基板と貼り合わせて評価用試料を得た。
21 バリア性層、タッチパネル層または表面保護層
22 封止層、オーバーコート層、またはバリア性層
23 平坦化層または封止層
24 バリア性層
50 基材層
100 表示装置
Claims (6)
- 重合性化合物および硬化剤を含有する表示素子用封止剤であって、
前記重合性化合物が、以下の成分(A)および(B):
(A)2官能以上の脂環構造を有する(メタ)アクリレート
(B)2官能の鎖状構造を有する(メタ)アクリレート
を含み、
前記成分(A)および(B)の合計100質量部に対して前記成分(A)の含有量が60質量部以下であり、
当該表示素子用封止剤中の成分(C):単官能の(メタ)アクリレートの含有量が、前記重合性化合物100質量部に対して1質量部以下である、表示素子用封止剤。 - 前記成分(A)が、ジメチロール-トリシクロデカンジ(メタ)アクリレートを含む、請求項1に記載の表示素子用封止剤。
- 前記成分(B)が、1,12-ドデカンジオールジ(メタ)アクリレート、1,9-ノナンジオールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレートおよびトリプロピレングリコールジ(メタ)アクリレートからなる群から選択される1または2以上の(メタ)アクリレートである、請求項1または2に記載の表示素子用封止剤。
- 有機EL表示素子の封止用である、請求項1乃至3いずれか1項に記載の表示素子用封止剤。
- 請求項1乃至4いずれか1項に記載の表示素子用封止剤を硬化してなる硬化物。
- 基板と、
前記基板上に配置された表示素子と、
前記表示素子を被覆する封止層と、
を含み、
前記封止層が、請求項1乃至4いずれか1項に記載の表示素子用封止剤の硬化物により構成されている、表示装置。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202180049407.1A CN115804245A (zh) | 2020-09-18 | 2021-09-16 | 显示元件用密封剂、其固化物和显示装置 |
KR1020237000656A KR20230022967A (ko) | 2020-09-18 | 2021-09-16 | 표시 소자용 봉지제, 그의 경화물 및 표시 장치 |
JP2022550606A JPWO2022059740A1 (ja) | 2020-09-18 | 2021-09-16 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2020157660 | 2020-09-18 | ||
JP2020-157660 | 2020-09-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2022059740A1 true WO2022059740A1 (ja) | 2022-03-24 |
Family
ID=80776699
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2021/034151 WO2022059740A1 (ja) | 2020-09-18 | 2021-09-16 | 表示素子用封止剤、その硬化物および表示装置 |
Country Status (5)
Country | Link |
---|---|
JP (1) | JPWO2022059740A1 (ja) |
KR (1) | KR20230022967A (ja) |
CN (1) | CN115804245A (ja) |
TW (1) | TW202214814A (ja) |
WO (1) | WO2022059740A1 (ja) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2017061606A (ja) * | 2015-09-24 | 2017-03-30 | Jsr株式会社 | 硬化性組成物、硬化物、硬化物の形成方法、積層体及び有機elデバイス |
WO2018051732A1 (ja) * | 2016-09-15 | 2018-03-22 | Jnc株式会社 | インク組成物およびこれを用いた有機電界発光素子 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019082996A1 (ja) | 2017-10-26 | 2019-05-02 | デンカ株式会社 | 有機エレクトロルミネッセンス表示素子用封止剤 |
-
2021
- 2021-09-16 WO PCT/JP2021/034151 patent/WO2022059740A1/ja active Application Filing
- 2021-09-16 KR KR1020237000656A patent/KR20230022967A/ko not_active Application Discontinuation
- 2021-09-16 CN CN202180049407.1A patent/CN115804245A/zh active Pending
- 2021-09-16 JP JP2022550606A patent/JPWO2022059740A1/ja active Pending
- 2021-09-17 TW TW110134820A patent/TW202214814A/zh unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2017061606A (ja) * | 2015-09-24 | 2017-03-30 | Jsr株式会社 | 硬化性組成物、硬化物、硬化物の形成方法、積層体及び有機elデバイス |
WO2018051732A1 (ja) * | 2016-09-15 | 2018-03-22 | Jnc株式会社 | インク組成物およびこれを用いた有機電界発光素子 |
Also Published As
Publication number | Publication date |
---|---|
CN115804245A (zh) | 2023-03-14 |
TW202214814A (zh) | 2022-04-16 |
JPWO2022059740A1 (ja) | 2022-03-24 |
KR20230022967A (ko) | 2023-02-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5785331B2 (ja) | 表示素子用封止剤 | |
KR20150105897A (ko) | 경화성 수지 조성물을 포함하는 배리어 적층체 및 이의 제조방법 | |
JP5895757B2 (ja) | 感光性組成物、成形物の製造方法、成形物および半導体装置 | |
JP2016066605A (ja) | 表示素子用封止剤 | |
JP5798259B1 (ja) | 表示素子用封止剤 | |
JP5957148B1 (ja) | 表示素子用封止剤 | |
JP2017054084A (ja) | 表示素子用封止剤 | |
WO2022059740A1 (ja) | 表示素子用封止剤、その硬化物および表示装置 | |
JP2016110788A (ja) | 表示素子用封止剤 | |
WO2016021531A1 (ja) | 表示素子用封止剤 | |
WO2022059738A1 (ja) | 表示素子用封止剤、その硬化物および表示装置 | |
JP2016074784A (ja) | 表示素子用封止剤 | |
JP2017045646A (ja) | 表示素子用封止剤 | |
JP2017103154A (ja) | 表示素子用封止剤 | |
JP2017117651A (ja) | 表示素子用封止剤 | |
JP2016169298A (ja) | 表示素子用封止剤 | |
JP2023044825A (ja) | 紫外線硬化性樹脂組成物 | |
JP6496214B2 (ja) | 表示素子用封止剤 | |
CN115768802B (zh) | 紫外线固化性树脂组合物 | |
WO2022050421A1 (ja) | インクジェット塗布用及びled保護用硬化性組成物、ledモジュール、ledモジュールの製造方法及びled表示装置 | |
WO2016063825A1 (ja) | 表示素子用封止剤及び表示素子用封止剤硬化体 | |
JP2016164236A (ja) | 表示素子用封止剤 | |
JP6595848B2 (ja) | 表示素子用封止剤 | |
JP2017002131A (ja) | 表示素子用封止剤 | |
JP2015218303A (ja) | 表示素子用透明封止剤 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 21869423 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 20237000656 Country of ref document: KR Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 2022550606 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 21869423 Country of ref document: EP Kind code of ref document: A1 |